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Entrepreneur Style T-Shirts

Hey Guys. I have been thinking about getting some t-shirts developed that are along the lines of the shirts that you would see at a bar or club that say security, only these would say entrepreneur on them with a line underneath saying 'mixing business with pleasure'

I am curious as to if people would be interested in such a thing.
As well, if anyone on this forum would want to order one if I were to get them created? Please see the attached image to see what they would look like. Right now it is just the back on a black shirt with nothing on the front. I am trying to think of something that could go on the front. Ideas?

I have what may or may not be a stupid idea.
A stick figure man holding a cocktail in one hand(the kind with a little umbrella in it) and brief case in the other. He's wearing a shirt & tie, and suit coat, but is wearing hawaiian style shorts, and maybe a straw panama hat.

If the guy had a suit jacket, shirt, tie, and shorts on, would he really be a stick figure then? i always think of stick figures as being straight lines with no added effects to them...but not a bad idea. perhaps i will try and work with that.

If the guy had a suit jacket, shirt, tie, and shorts on, would he really be a stick figure then? i always think of stick figures as being straight lines with no added effects to them...but not a bad idea. perhaps i will try and work with that.

You're right. At first, in my mind, I imagined a simple stick figure with a round head, a stick body, stick arms and legs, and just holding a drink and brief case. But as I went on typing I kept adding things. The only thing that would really be showing are his legs and feet. I'd probably leave the hat off to show the head as well. Stick figures are really cute, I don't know why, they just are, so I'd probably show enough of him so that you could tell he was a stick figure.

I've actually been thinking about looking into starting my own line of t-shirts, bumper stickers, etc (printed stuff), because I think I can come up with a bunch of goofy ideas that people might buy into. It seems it's always the silliest ideas that do the best with those types of products. But the prospect of having to deal with copyrights, trademarks, etc, seems kind of daunting. (Don't you have to check to make sure that you aren't inadvertently using something that's copyrighted?)

there is a lot that can go into having your own line of printed items (clothing, mugs, etc) which i am not completely sure of as I am not trying to do a full line of items. This was just an idea that came to me and thought that would be cool to do and people would be interested in. As far as i know, the word entrepreneur is not copywritted by anyone person, so all should be well.